Modulating N- versus O-arylation in pyrazolone-aryl halide couplings

Tetrahedron Letters

Volumn 49, Issue 5, 2008, Pages 794-798

  Golden, Jennifer E ^a   Sanders, Shanina D ^a   Muller, Kristine M ^a   Bürli, Roland W ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HALOPYRIDINE DERIVATIVE; COPPER; HALIDE; PYRAZOLE; PYRAZOLONE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 37649023243     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.185     Document Type: Article

References (18)

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2. Banner, B.; Lester; B.; Joseph A.; Fotouhi, N.; Gillespie, P.; Goodnow, R. A.; Hamilton, M. M.; Haynes, N.-E.; Kowalczyk, A.; Mayweg, A.; Myers, M. P.; Pietranico-Cole, S. L.; Scott, N. R.; Thakkar, K. C.; Tilley, J. W. U.S. Patent Appl. 2,007,049,632, 2007.
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8. More recently, an example of a Pd-catalyzed N-arylation of a structurally related pyrazolidinone was reported. Sibi M.P., Manyem S., and Palencia H. J. Am. Chem. Soc. 128 (2006) 13660-13661
9. Pyrazolone 3 was prepared according to a modified procedure. See Supplementary data, and Ref. 2b.
10. For N-arylation of amides, see:. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727-7729
11. Klapars A., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 7421-7428
12. For N-arylation of acyl hydrazines, see:. Wolter M., Klapars A., and Buchwald S.L. Org. Lett. 3 (2001) 3803-3805
13. The reaction of 2-chloropyridines with N-alkylated pyrazole derivatives similar to 3 is known to afford the corresponding O-aryl pyrazoles with CuI, DMF and heating at 100 °C. Importantly in this example, only pyrazole O-aryl products can result, as the acyl ring nitrogen is already alkylated; see: Morimoto, K.; Oonari, M.; Furusawa, H.; Hatanaka, M.; Watanabe, J.; Kondo, Y.; Nawamaki, T.; Ishikawa, K.; Shiojima, K.; Nakahira, K. Patent JP 07285962, 1995.
14. Selwood D.L., Brummell D.G., Budworth J., Burtin G.E., Campbell R.O., Chana S.S., Charles I.G., Fernandez P.A., Glen R.C., Goggin M.C., Hobbs A.J., Kling M.R., Liu Q., Madge D.J., Millerais S., Powell K.L., Reynolds K., Spacey G.D., Stables J.N., Tatlock M.A., Wheeler K.A., Wishart G., and Woo C.-K. J. Med. Chem. 44 (2001) 78-93
15. Summarized results from the entire array of screened reactions can be found in the Supplementary data.
16. Schlosser M., and Cottet F. Eur. J. Org. Chem. (2002) 4181-4184
17. ++H) m/z calculated: 218.1288, found: 218.1281.
18. ++Na) m/z calculated: 240.1107, found: 240.1102.